Organoboron complexes and their use in organic electroluminescent devices

ABSTRACT

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a national stage application (under 35 U.S.C. § 371)of PCT/EP2018/061767, filed May 8, 2018, which claims benefit ofEuropean Application No. 17170654.2, filed May 11, 2017, both of whichare incorporated herein by reference in their entirety.

The present invention relates to a compound of the formula (1), to theuse of the compound in an electronic device, and to an electronic devicecomprising a compound of the formula (1). The present inventionfurthermore relates to a process for the preparation of a compound ofthe formula (1) and to a formulation comprising one or more compounds ofthe formula (1).

The structure of organic electroluminescent devices (OLEDs) in whichorganic semiconductors are employed as functional materials isdescribed, for example, in U.S. Pat. No. 4,539,507. The emittingmaterials employed here are very often organometallic complexes whichexhibit phosphorescence. For quantum-mechanical reasons, an up tofour-fold increase in efficiency is possible using phosphorescentinstead of fluorescent emitters. In general, however, there is still aneed for improvement in the case of OLEDs, in particular also in thecase of OLEDs which exhibit triplet emission (phosphorescence), forexample with respect to efficiency, operating voltage and lifetime.

The properties of phosphorescent OLEDs are not only determined by thetriplet emitters employed but also by the other materials used togetherwith triplet emitters in OLEDs, such as matrix materials, also calledhost materials. Improvements in these materials and theircharge-transport properties can thus also result in significantimprovements in the OLED properties.

Thus, the choice of the matrix material in an emission layer comprisinga phosphorescent emitter has a great influence on OLEDs properties,especially in terms of efficiency. The matrix material limits thequenching of excited states of emitter molecules by energy transfer.

The object of the present invention is the provision of compounds, whichare suitable for use in an OLED, in particular as matrix material forphosphorescent emitters. A further object of the present invention is toprovide further organic semiconductors for organic electroluminescentdevices to provide the person skilled in the art with a greater possiblechoice of materials for the production of OLEDs.

Organoboron complexes are known from the prior art for their opticalproperties (for example in Más-Montoya et al., J. Org. Chem. 2016, 81,3296-3302 and in Liu et al., Adv. Funct. Mater. 2005, 15, No. 1,January, 143-154).

Surprisingly, it has been found that certain organoboron complexesdescribed in greater detail below are highly suitable for use in OLEDs,in particular as matrix material for phosphorescent emitters. Whenemployed as matrix materials, these compounds lead to OLEDs exhibitingvery good properties in terms of lifetime and/or efficiency and/orelectroluminescent emission. In addition, these compounds have a highglass transition temperature and a good thermal stability, which is animportant property for OLED materials, especially when the materials arevapor-deposited via a vacuum process.

The present invention therefore relates to these compounds and toelectronic devices, in particular organic electroluminescent devices,which comprise compounds of this type.

The present invention relates to a compound of the formula (1):

where the following applies to the symbols and indices used:

Ar¹ is a heteroaryl group comprising at least one nitrogen which isrepresented in formula (1), having 5 to 30 aromatic ring atoms, whichmay be substituted by one or more radicals R¹;

X stands, on each occurrence, identically or differently, for CR² or N;or two adjacent groups X form together a ring condensed on the structureof formula (1), wherein the condensed ring is selected from an aryl orheteroaryl group having 5 to 30 aromatic ring atoms, which may besubstituted by one or more radicals R²;

Ar^(B) is, on each occurrence, identically or differently, an aromaticor heteroaromatic ring system having 5 to 60 aromatic ring atoms, whichmay be substituted by one or more radicals R³;

W is on each occurrence, identically or differently, CR¹ or N; or twoadjacent groups W stand for a group of formula (W-1) or (W-2),

where the dashed bonds indicate the bonding to the groups of formula(1);

Z is on each occurrence, identically or differently, CR¹ or N;

E¹, E² are, on each occurrence, identically or differently, selectedfrom a single bond, B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰, C═C(R⁰)₂, O, S,S═O, SO₂, N(R⁰), P(R⁰) and P(═O)R⁰, where at least one of the groups E¹and E², present in the same ring, is not a single bond;

R⁰ stands on each occurrence, identically or differently, for H, D, F,Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkylgroups having 3 to 40 C atoms, each of which may be substituted by oneor more radicals R⁴, where in each case one or more non-adjacent CH₂groups may be replaced by R⁴C═CR⁴, C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O,C═S, C═Se, P(═O)(R⁴), SO, SO₂, O, S or CONR⁴ and where one or more Hatoms may be replaced by D, F, Cl, Br, I, CN or NO₂, an aromatic orheteroaromatic ring systems having 5 to 60 aromatic ring atoms, whichmay in each case be substituted by one or more radicals R⁴, or anaryloxy groups having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴, where two adjacent substituentsR⁰ may form an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴;

R¹, R², R³ stand on each occurrence, identically or differently, for H,D, F, C, Br, I, CHO, CN, C(═O)Ar³, P(═O)(Ar³)₂, S(═O)Ar³, S(═O)₂Ar³,N(Ar³)₂, NO₂, Si(R⁴)₃, B(OR⁴)₂, OSO₂R⁴, a straight-chain alkyl, alkoxyor thioalkyl groups having 1 to 40 C atoms or branched or a cyclicalkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of whichmay be substituted by one or more radicals R⁴, where in each case one ormore non-adjacent CH₂ groups may be replaced by R⁴C═CR⁴, C≡C, Si(R⁴)₂,Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴), SO, SO₂, O, S or CONR⁴ andwhere one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO₂,an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ringatoms, which may in each case be substituted by one or more radicals R⁴,or an aryloxy groups having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴; where two adjacent substituentsR¹, two adjacent substituents R² and/or two adjacent substituents R³ mayform an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴;

Ar³ is, on each occurrence, identically or differently, an aromatic orheteroaromatic ring system having 5 to 60 aromatic ring atoms, which mayin each case also be substituted by one or more radicals R⁴;

R⁴ stands on each occurrence, identically or differently, for H, D, F,Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groupshaving 3 to 20 C atoms, where in each case one or more non-adjacent CH₂groups may be replaced by SO, SO₂, O, S and where one or more H atomsmay be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromaticring system having 5 to 24 C atoms.

Adjacent substituents in the sense of the present invention aresubstituents which are bonded to carbon atoms which are linked directlyto one another or which are bonded to the same carbon atom.

Furthermore, the following definitions of chemical groups apply for thepurposes of the present application:

An aryl group in the sense of this invention contains 6 to 60 aromaticring atoms; a heteroaryl group in the sense of this invention contains 5to 60 aromatic ring atoms, at least one of which is a heteroatom. Thehetero atoms are preferably selected from N, O and S. This representsthe basic definition. If other preferences are indicated in thedescription of the present invention, for example with respect to thenumber of aromatic ring atoms or the heteroatoms present, these apply.

An aryl group or heteroaryl group here is taken to mean either a simplearomatic ring, i.e. benzene, or a simple heteroaromatic ring, forexample pyridine, pyrimidine or thiophene, or a condensed (annellated)aromatic or heteroaromatic polycycle, for example naphthalene,phenanthrene, quinoline or carbazole. A condensed (annellated) aromaticor heteroaromatic polycycle in the sense of the present applicationconsists of two or more simple aromatic or heteroaromatic ringscondensed with one another.

An aryl or heteroaryl group, which may in each case be substituted bythe above-mentioned radicals and which may be linked to the aromatic orheteroaromatic ring system via any desired positions, is taken to mean,in particular, groups derived from benzene, naphthalene, anthracene,phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene,benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene,furan, benzofuran, isobenzofuran, dibenzofuran, thiophene,benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole,isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine,phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline,benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole,imidazole, benzimidazole, naphthimidazole, phenanthrimidazole,pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole,benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole,1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine,pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine,naphthyridine, azacarbazole, benzocarboline, phenanthroline,1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole,1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole,1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine,1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine,1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine andbenzothiadiazole.

An aryloxy group in accordance with the definition of the presentinvention is taken to mean an aryl group, as defined above, which isbonded via an oxygen atom. An analogous definition applies toheteroaryloxy groups.

An aromatic ring system in the sense of this invention contains 6 to 60C atoms in the ring system. A heteroaromatic ring system in the sense ofthis invention contains 5 to 60 aromatic ring atoms, at least one ofwhich is a heteroatom. The heteroatoms are preferably selected from N, Oand/or S.

An aromatic or heteroaromatic ring system in the sense of this inventionis intended to be taken to mean a system which does not necessarilycontain only aryl or heteroaryl groups, but instead in which, inaddition, a plurality of aryl or heteroaryl groups may be connected by anon-aromatic unit (preferably less than 10% of the atoms other than H),such as, for example, an sp³-hybridised C, Si, N or O atom, ansp²-hybridised C or N atom or an sp-hybridised C atom. Thus, forexample, systems such as 9,9′-spirobifluorene, 9,9′-diarylfluorene,triarylamine, diaryl ether, stilbene, etc., are also intended to betaken to be aromatic ring systems in the sense of this invention, as aresystems in which two or more aryl groups are connected, for example, bya linear or cyclic alkyl, alkenyl or alkynyl group or by a silyl group.Furthermore, systems in which two or more aryl or heteroaryl groups arelinked to one another via single bonds are also taken to be aromatic orheteroaromatic ring systems in the sense of this invention, such as, forexample, systems such as biphenyl, terphenyl or diphenyltriazine.

An aromatic or heteroaromatic ring system having 5-60 aromatic ringatoms, which may in each case also be substituted by radicals as definedabove and which may be linked to the aromatic or heteroaromatic groupvia any desired positions, is taken to mean, in particular, groupsderived from benzene, naphthalene, anthracene, benzanthracene,phenanthrene, benzophenanthrene, pyrene, chrysene, perylene,fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl,biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene,spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene,cis- or trans-indenofluorene, truxene, isotruxene, spirotruxene,spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran,thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole,indole, isoindole, carbazole, indolocarbazole, indenocarbazole,pyridine, quinoline, isoquinoline, acridine, phenanthridine,benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline,phenothiazine, phenoxazine, pyrazole, indazole, imidazole,benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole,pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole,naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole,1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine,benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene,2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene,4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine,phenothiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline,phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole,1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole,1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole,1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine,tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine,purine, pteridine, indolizine and benzothiadiazole, or combinations ofthese groups.

For the purposes of the present invention, a straight-chain alkyl grouphaving 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, inwhich, in addition, individual H atoms or CH₂ groups may be substitutedby the groups mentioned above under the definition of the radicals, ispreferably taken to mean the radicals methyl, ethyl, n-propyl, i-propyl,n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl,cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl,cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl,pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl,pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl,octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl oroctynyl. An alkoxy or thioalkyl group having 1 to 40 C atoms ispreferably taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy,i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy,2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy,n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy,2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio,i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio,n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio,cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio,trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio,ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio,hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio,octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio,pentynylthio, hexynylthio, heptynylthio or octynylthio.

The formulation that two radicals may form a ring with one another is,for the purposes of the present application, intended to be taken tomean, inter alia, that the two radicals are linked to one another by achemical bond. This is illustrated by the following schemes:

Furthermore, the above-mentioned formulation is also intended to betaken to mean that, in the case where one of the two radicals representshydrogen, the second radical is bonded at the position to which thehydrogen atom was bonded, with formation of a ring. This is illustratedby the following scheme:

In accordance with a preferred embodiment of the invention, the groupAr¹ is a heteroaryl group having 5 to 18 aromatic ring atoms. Morepreferably, the group Ar¹ is selected from the groups of formulae(Ar1-1) or (Ar1-2),

where the sign * indicates the position of the coordination to the Boronand the sign {circumflex over ( )} indicates the bonds to the adjacent6-membered ring, as depicted in formula (1), and the symbol W has thesame meaning as above.

In accordance with a preferred embodiment of the invention, E¹, E² are,on each occurrence, identically or differently, selected from a singlebond, C(R⁰)₂, C═O, O, S, S═O, SO₂ and N(R⁰), where at least one of thegroups E¹ and E², present in the same ring, is not a single bond. Verypreferably, one of the groups E¹ and E² is a single bond and the otherone is C(R⁰)₂, C═O, O, S, S═O, SO₂ or N(R⁰). Particularly preferably,one of the groups E¹ and E² is a single bond and the other one isC(R⁰)₂, O, S, or N(R⁰).

Preferably, R⁰ stands on each occurrence, identically or differently,for H, D, F, a straight-chain alkyl group having 1 to 10 C atoms orbranched or a cyclic alkyl group having 3 to 10 C atoms, each of whichmay be substituted by one or more radicals R⁴, where one or more H atomsmay be replaced by D or F, an aromatic or heteroaromatic ring systemshaving 5 to 18 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴, where two adjacent substituentsR⁰ may form an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴.

In accordance with a preferred embodiment of the invention, X stands, oneach occurrence, identically or differently, for CR² or N; or twoadjacent groups X form together a ring condensed on the structure offormula (1), wherein the condensed ring is selected from formulae (X-1)and (X-2),

where the dashed bonds indicate the bonding of the correspondingadjacent groups X to the structure of formula (1);

V is on each occurrence, identically or differently, CR² or N; or twoadjacent groups V form together a ring condensed on the structure offormula (X-1) or formula (X-2), wherein the condensed ring is selectedfrom formulae (V-1) and (V-2),

where the dashed bonds indicate the bonding of the correspondingadjacent groups V to the structures of formulae (X-1) and (X-2);U is on each occurrence, identically or differently, CR² or N; andE¹, E² and R² have the same meaning as above.

In accordance with a preferred embodiment, the compound of formula (1)is selected from the compounds of formula (2),

where the symbols Ar^(B), X and W have the same meaning as above.

In accordance with a preferred embodiment, the compounds of formula (1)or (2) are selected from the compounds of formulae (3) to (6),

where the symbols Ar^(B), W, V, E¹, E² and R² have the same meaning asabove.

Preferably, there is maximum one group X in the 5-membered ring asdepicted in formula (1) which stands for N, there are maximum two groupsW per 6-membered ring, which stand for N, there are maximum two groups Vper 6-membered ring, which stand for N, there are maximum two groups Zper 6-membered ring, which stand for N and there are maximum two groupsT per 6-membered ring, which stand for N.

In accordance with a preferred embodiment, the compounds of formula (1)to (6) are selected from the compounds of formulae (3-1) to (6-2),

where the symbols Ar^(B), R¹ and R² have the same meaning as above andwhere E¹ in formula (6-1) is B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰,C═C(R⁰)₂, O, S, S═O, SO₂, N(R⁰), P(R⁰) or P(═O)R⁰.

In accordance with a preferred embodiment, the group Ar^(B) is, on eachoccurrence, identically or differently, an aromatic or heteroaromaticring system having 5 to 30 aromatic ring atoms, more preferably 5 to 18aromatic ring atoms, which may be substituted by one or more radicalsR³. It is very preferably that Ar^(B) is, on each occurrence,identically or differently, an aromatic ring system having 6 to 18aromatic ring atoms, more preferably 6 to 12 aromatic ring atoms, whichmay be substituted by one or more radicals R³. Examples of very suitablegroups for Ar^(B) are phenyl, biphenyl and naphthyl groups, which may besubstituted by one or more radicals R³.

Preferably, R¹, R² stand on each occurrence, identically or differently,for H, D, F, CN, N(Ar³)₂, a straight-chain alkyl group having 1 to 20 Catoms or branched or a cyclic alkyl group having 3 to 20 C atoms, eachof which may be substituted by one or more radicals R⁴, where in eachcase one or more non-adjacent CH₂ groups may be replaced by R⁴C═CR⁴,C═O, O or S and where one or more H atoms may be replaced by D or F, anaromatic or heteroaromatic ring systems having 5 to 40 aromatic ringatoms, preferably 5 to 25 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴; where two adjacent substituentsR¹ and/or two adjacent substituents R² may form an aliphatic or aromaticring system together, which may be substituted by one or more radicalsR⁴.

Preferably, R³ stands on each occurrence, identically or differently,for H, D, F, CN, N(Ar³)₂, a straight-chain alkyl group having 1 to 20 Catoms or branched or a cyclic alkyl group having 3 to 20 C atoms, eachof which may be substituted by one or more radicals R⁴, where in eachcase one or more non-adjacent CH₂ groups may be replaced by R⁴C═CR⁴,C═O, O or S and where one or more H atoms may be replaced by D or F, anaromatic or heteroaromatic ring systems having 5 to 40 aromatic ringatoms, preferably 5 to 25 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴; where two adjacent substituentsR³ may form an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴. Very preferably, R³ stands oneach occurrence, identically or differently, for H, D, F, astraight-chain alkyl group having 1 to 10 C atoms or branched or acyclic alkyl group having 3 to 10 C atoms, each of which may besubstituted by one or more radicals R⁴, where one or more H atoms may bereplaced by D or F, an aromatic or heteroaromatic ring systems having 5to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, verypreferably 5 to 18 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴.

In accordance with a preferred embodiment, the compounds of formulae(1), (2), (3) to (6) and (3-1) to (6-2) comprise at least one group R¹or R² selected from aromatic or heteroaromatic ring systems having 5 to60 aromatic ring atoms, which may in each case be substituted by one ormore radicals R⁴.

More preferably, the compounds of formulae (1), (2), (3) to (6) and(3-1) to (6-2) comprise at least one group R¹ or R² selected from thegroups of formulae (R-1) to (R-15),

where:the dashed bond indicates the bonding to the structure of formulae (1),(2), (3) to (6) and (3-1) to (6-2) and the symbol V has the same meaningas above, with the proviso that V is a C atom when the dashed bond isbonded to V, and where:

R^(N), R^(C) are on each occurrence, identically or differently, H, D,F, Cl, Br, I, CHO, N(Ar³)₂, C(═O)Ar³, P(═O)(Ar³)₂, S(═O)Ar³, S(═O)₂Ar³,(R)C═C(R)Ar³, CN, NO₂, Si(R⁴)₃, B(OR⁴)₂, B(R⁴)₂, B(N(R⁴)₂)₂, OSO₂R⁴, astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atomsor a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or abranched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy grouphaving 3 to 40 C atoms, each of which may be substituted by one or moreradicals R⁴, where one or more, preferably non-adjacent CH₂ groups maybe replaced by (R⁴)C═C(R⁴), C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S,C═Se, P(═O)(R⁴), SO, SO₂, N(R⁴), O, S or CON(R⁴) and where one or more Hatoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system having 5 to 60 aromatic ring atoms, which mayin each case be substituted by one or more radicals R⁴, or an aryloxy orheteroaryloxy group having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴, where optionally two adjacentsubstituents R^(C) can form a mono- or polycyclic, aliphatic, aromaticor heteroaromatic ring system with one another; where Ar³ and R⁴ havethe same definitions as above; and T stands, on each occurrence,identically or differently, for CR⁴ or N, with the proviso that T is a Catom when the dashed bond is bonded to T; or two adjacent groups T standfor a group of formula (T-1) or (T-2),

where the dashed bonds in formulae (T-1) and (T-2) indicate the bondingto the groups of formulae (R-1) to (R-5);

G is on each occurrence, identically or differently, CR⁴ or N; where R⁴has the same meaning as above;

L is an aromatic or heteroaromatic ring system having 5 to 30 aromaticring atoms, which may be substituted by one or more radicals R⁴;

n is 0 or 1, preferably 0.

L is preferably an aromatic or heteroaromatic ring system having 5 to 18aromatic atoms, which may be substituted by one or more radicals R⁴. Lis very preferably an aromatic ring system having 6 to 12 aromaticatoms, which may be substituted by one or more radicals R⁴. L isparticularly preferably a phenyl group, which may be substituted by oneor more radicals R.

Examples of suitable groups R¹ or R² of formulae (R-1) to (R-15) aregroups of formulae (R-16) to (R-129),

where

the dashed bond indicates the bonding to the group of formulae (1), (2),(3) to (6) or (3-1) to (6-2);

E, R^(N) and R^(C) have the same meaning as above; and the groups offormulae (R-16) to (R-129) are optionally substituted by one or moreradicals R⁴ at any free positions.

Among formulae (R-1) to (R-15), formulae (R-1), (R-2), (R-4), (R-5) and(R-8) to (R-12) are preferred.

Among formulae (R-16) to (R-129), formulae (R-16), (R-19), (R-22) to(R-33), (R-42), (R-44), (R-55), (R-56), (R-68), (R-71), (R-72), (R-76)to (R-78), (R-93), (R-94), (R-96), (R-101) to (R-108), (R-120), (R-123),(R-125), (R-126), (R-128) and (R-129) are preferred.

The group R^(C) according to the present invention is preferablyselected on each occurrence, identically or differently, from the groupconsisting of H, D, F, CN, Si(R⁴)₃, a straight-chain alkyl group having1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 Catoms, each of which may be substituted by one or more radicals R⁴, anaromatic or heteroaromatic group having 5 to 25 aromatic ring atoms,each of which may be substituted by one or more radicals R⁴, where twoadjacent substituents Re may optionally form a mono- or polycyclic,aliphatic ring system or aromatic ring system, each of which may besubstituted by one or more radicals R⁴. More preferably, R^(C) isselected on each occurrence, identically or differently, from the groupconsisting of H, a straight-chain alkyl group having 1 to 5 C atoms or abranched or cyclic alkyl group having 3 to 5 C atoms, each of which maybe substituted by one or more radicals R⁴, an aryl or heteroaryl grouphaving 5 to 18 aromatic ring atoms, each of which may be substituted byone or more radicals R⁴.

The group R^(N) according to the invention is preferably selected oneach occurrence, identically or differently, from the group consistingof a straight-chain alkyl group having 1 to 10 C atoms or a branched orcyclic alkyl group having 3 to 10 C atoms, each of which may besubstituted by one or more radicals R⁴, an aromatic or heteroaromaticring system having 5 to 25 aromatic ring atoms, each of which may besubstituted by one or more radicals R⁴. More preferably, R^(N) is anaromatic or heteroaromatic ring system having 5 to 25 aromatic ringatoms, preferably 6 to 18 aromatic ring atoms, more preferably 6 to 13aromatic ring atoms. The group R^(N) is particularly preferably selectedfrom the group consisting of phenyl, biphenyl, terphenyl, pyridine,quinoline, isoquinoline, pyridazine, benzopyridazine, pyrimidine,benzopyrimidine, benzimidazole, quinoxaline, pyrazine, 1,3,5-triazine,1,2,4-triazine or 1,2,3-triazine, each of which may be substituted byone or more radicals R⁴.

Examples of suitable compounds according to the invention are thestructures shown in the table below:

The compounds according to the invention can be prepared by synthesissteps known to the person skilled in the art, such as, for example,bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwaldcoupling, etc.

Suitable synthesis processes are depicted in general terms in Scheme 1below.

The present invention therefore furthermore relates to a process for thesynthesis of the compounds according to the invention, wherein acompound of formula (Int) reacts with a triarylborane B(Ar^(B))₃ so thata compound of formula (1) is obtained as depicted in scheme 1 above, andwhere the symbols Ar¹, Ar^(B), W and X have the same meaning as above.For the processing of the compounds according to the invention from theliquid phase, for example by spin coating or by printing processes,formulations of the compounds according to the invention are necessary.These formulations can be, for example, solutions, dispersions oremulsions. It may be preferred to use mixtures of two or more solventsfor this purpose. Suitable and preferred solvents are, for example,toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene,tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane,phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone,1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene,1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol,2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole,3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene,decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP,p-cymene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethyleneglycol butyl methyl ether, triethylene glycol butyl methyl ether,diethylene glycol dibutyl ether, triethylene glycol dimethyl ether,diethylene glycol-monobutyl ether, tripropylene glycol dimethyl ether,tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene,pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene,1,1-bis(3,4-dimethylphenyl)ethane or mixtures of these solvents.

The present invention therefore furthermore relates to a formulationcomprising a compound according to the invention and at least onefurther compound. The further compound may be, for example, a solvent,in particular one of the above-mentioned solvents or a mixture of thesesolvents. However, the further compound may also be at least one furtherorganic or inorganic compound which is likewise employed in theelectronic device, for example an emitting compound, in particular aphosphorescent dopant, and/or a further matrix material. Suitableemitting compounds and further matrix materials are indicated below inconnection with the organic electroluminescent device. This furthercompound may also be polymeric.

The compounds and mixtures according to the invention are suitable foruse in an electronic device. An electronic device here is taken to meana device which comprises at least one layer which comprises at least oneorganic compound. However, the component here may also compriseinorganic materials or also layers built up entirely from inorganicmaterials.

The present invention therefore furthermore relates to the use of thecompounds or mixtures according to the invention in an electronicdevice, in particular in an organic electroluminescent device.

The present invention again furthermore relates to an electronic devicecomprising at least one of the compounds or mixtures according to theinvention mentioned above. The preferences stated above for the compoundalso apply to the electronic devices.

The electronic device is preferably selected from the group consistingof organic electroluminescent devices (OLEDs, PLEDs), organic integratedcircuits (O-ICs), organic field-effect transistors (O-FETs), organicthin-film transistors (O-TFTs), organic light-emitting transistors(O-LETs), organic solar cells (O-SCs), organic dye-sensitised solarcells, organic optical detectors, organic photoreceptors, organicfield-quench devices (O-FQDs), light-emitting electrochemical cells(LECs), organic laser diodes (O-lasers) and “organic plasmon emittingdevices” (D. M. Koller et al., Nature Photonics 2008, 1-4), preferablyorganic electroluminescent devices (OLEDs, PLEDs), in particularphosphorescent OLEDs.

The organic electroluminescent device comprises a cathode, an anode andat least one emitting layer. Apart from these layers, it may alsocomprise further layers, for example in each case one or morehole-injection layers, hole-transport layers, hole-blocking layers,electron-transport layers, electron-injection layers, exciton-blockinglayers, electron-blocking layers and/or charge-generation layers. It islikewise possible for interlayers, which have, for example, anexciton-blocking function, to be introduced between two emitting layers.However, it should be pointed out that each of these layers does notnecessarily have to be present. The organic electroluminescent devicehere may comprise one emitting layer or a plurality of emitting layers.If a plurality of emission layers are present, these preferably have intotal a plurality of emission maxima between 380 nm and 750 nm,resulting overall in white emission, i.e. various emitting compoundswhich are able to fluoresce or phosphoresce are used in the emittinglayers. Particular preference is given to systems having three emittinglayers, where the three layers exhibit blue, green and orange or redemission (for the basic structure see, for example, WO 2005/011013).These can be fluorescent or phosphorescent emission layers or hybridsystems, in which fluorescent and phosphorescent emission layers arecombined with one another.

The compound according to the invention in accordance with theembodiments indicated above can be employed in various layers, dependingon the precise structure. Preference is given to an organicelectroluminescent device comprising a compound of the formula (1) or inaccordance with the preferred embodiments as matrix material forfluorescent emitters, phosphorescent emitters or emitters showing TADF(Thermally Activated Delayed Fluorescence), in particular forphosphorescent emitters, and/or in an electron-transport layer and/or inan electron-blocking or exciton-blocking layer and/or in ahole-transport layer, depending on the precise substitution. Thepreferred embodiments indicated above also apply to the use of thematerials in organic electronic devices.

In a preferred embodiment of the invention, the compound of the formula(1) or in accordance with the preferred embodiments is employed asmatrix material for a fluorescent or phosphorescent compound, inparticular for a phosphorescent compound, in an emitting layer. Theorganic electroluminescent device here may comprise one emitting layeror a plurality of emitting layers, where at least one emitting layercomprises at least one compound according to the invention as matrixmaterial.

If the compound of the formula (1) or in accordance with the preferredembodiments is employed as matrix material for an emitting compound inan emitting layer, it is preferably employed in combination with one ormore phosphorescent materials (triplet emitters). Phosphorescence in thesense of this invention is taken to mean the luminescence from anexcited state having spin multiplicity>1, in particular from an excitedtriplet state. For the purposes of this application, all luminescenttransition-metal complexes and luminescent lanthanide complexes, inparticular all iridium, platinum and copper complexes, are to beregarded as phosphorescent compounds.

Preferably, when the compounds of the formula (1) or in accordance withthe preferred embodiments are employed as matrix materials for anemitting compound in an emitting layer, they are preferably employed incombination with one or more phosphorescent material (triplet emitters),where the phosphorescent material has an emission wavelength comprisedbetween 550 nm to 680 nm, which corresponds to the red emission field.

The mixture comprising the compound of the formula (1) or in accordancewith the preferred embodiments and the emitting compound comprisesbetween 99 and 1% by vol., preferably between 98 and 10% by vol.,particularly preferably between 97 and 60% by vol., in particularbetween 95 and 80% by vol., of the compound of the formula (1) or inaccordance with the preferred embodiments, based on the entire mixturecomprising emitter and matrix material. Correspondingly, the mixturecomprises between 1 and 99% by vol., preferably between 2 and 90% byvol., particularly preferably between 3 and 40% by vol., in particularbetween 5 and 20% by vol., of the emitter, based on the entire mixturecomprising emitter and matrix material. A further preferred embodimentof the present invention is the use of the compound of the formula (1)or in accordance with the preferred embodiments as matrix material for aphosphorescent emitter in combination with a further matrix material.Particularly suitable matrix materials which can be employed incombination with the compounds of the formula (1) or in accordance withthe preferred embodiments are aromatic ketones, aromatic phosphineoxides or aromatic sulfoxides or sulfones, for example in accordancewith WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680,triarylamines, carbazole derivatives, for example CBP(N,N-biscarbazolylbiphenyl) or the carbazole derivatives disclosed in WO2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO2008/086851, indolocarbazole derivatives, for example in accordance withWO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, forexample in accordance with WO 2010/136109 and WO 2011/000455,azacarbazole derivatives, for example in accordance with EP 1617710, EP1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, forexample in accordance with WO 2007/137725, silanes, for example inaccordance with WO 005/111172, azaboroles or boronic esters, for examplein accordance with WO 2006/117052, triazine derivatives, for example inaccordance with WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinccomplexes, for example in accordance with EP 652273 or WO 2009/062578,diazasilole or tetraazasilole derivatives, for example in accordancewith WO 2010/054729, diazaphosphole derivatives, for example inaccordance with WO 2010/054730, bridged carbazole derivatives, forexample in accordance with US 2009/0136779, WO 2010/050778, WO2011/042107, WO 2011/088877 or in accordance with EP 11003232.3,triphenylene derivatives, for example in accordance with WO 2012/048781,or lactams, for example in accordance with WO 2011/116865 or WO2011/137951. A further phosphorescent emitter which emits at shorterwavelength than the actual emitter may likewise be present in themixture as co-host.

Preferred co-host materials are triarylamine derivatives, in particularmonoamines, lactams, carbazole derivatives and indenocarbazolederivatives.

Suitable phosphorescent compounds (=triplet emitters) are, inparticular, compounds which emit light, preferably in the visibleregion, on suitable excitation and in addition contain at least one atomhaving an atomic number greater than 20, preferably greater than 38 andless than 84, particularly preferably greater than 56 and less than 80,in particular a metal having this atomic number. The phosphorescentemitters used are preferably compounds which contain copper, molybdenum,tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium,platinum, silver, gold or europium, in particular compounds whichcontain iridium or platinum. For the purposes of the present invention,all luminescent compounds which contain the above-mentioned metals areregarded as phosphorescent compounds.

Examples of the emitters described above are revealed by theapplications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645,EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US2005/0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO2010/102709, WO 2011/032626, WO 2011/066898, WO 2011/157339, WO2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094962, WO2014/094961, WO 2014/094960 or WO 2016/124304. In general, allphosphorescent complexes as used in accordance with the prior art forphosphorescent OLEDs and as are known to the person skilled in the artin the area of organic electroluminescence are suitable, and the personskilled in the art will be able to use further phosphorescent complexeswithout inventive step.

Suitable phosphorescent materials (=triplet emitters) that can beadvantageously combined with the compounds of formula (1) are, asmentioned above, compounds which emit a red light on suitableexcitation, which means phosphorescent materials having an excitedtriplet state level (T1) comprised between 550 and 680 nm.

In a further embodiment of the invention, the organic electroluminescentdevice according to the invention does not comprise a separatehole-injection layer and/or hole-transport layer and/or hole-blockinglayer and/or electron-transport layer, i.e. the emitting layer isdirectly adjacent to the hole-injection layer or the anode, and/or theemitting layer is directly adjacent to the electron-transport layer orthe electron-injection layer or the cathode, as described, for example,in WO 2005/053051. It is furthermore possible to use a metal complexwhich is identical or similar to the metal complex in the emitting layeras hole-transport or hole-injection material directly adjacent to theemitting layer, as described, for example, in WO 2009/030981.

It is furthermore possible to employ the compounds according to theinvention in a hole-blocking or electron-transport layer. This applies,in particular, to compounds according to the invention which do not havea carbazole structure. These may preferably also be substituted by oneor more further electron-transporting groups, for example benzimidazolegroups.

In the further layers of the organic electroluminescent device accordingto the invention, it is possible to use all materials as usuallyemployed in accordance with the prior art. The person skilled in the artwill therefore be able, without inventive step, to employ all materialsknown for organic electroluminescent devices in combination with thecompounds of the formula (1) or in accordance with the preferredembodiments.

Preference is furthermore given to an organic electroluminescent device,characterised in that one or more layers are applied by means of asublimation process, in which the materials are vapour-deposited invacuum sublimation units at an initial pressure of less than 10⁻⁵ mbar,preferably less than 10⁻⁶ mbar. However, it is also possible for theinitial pressure to be even lower or higher, for example less than 10⁻⁷mbar.

Preference is likewise given to an organic electroluminescent device,characterised in that one or more layers are applied by means of theOVPD (organic vapour phase deposition) process or with the aid ofcarrier-gas sublimation, in which the materials are applied at apressure between 10⁻⁵ mbar and 1 bar. A special case of this process isthe OVJP (organic vapour jet printing) process, in which the materialsare applied directly through a nozzle and thus structured (for exampleM. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

Preference is furthermore given to an organic electroluminescent device,characterised in that one or more layers are produced from solution,such as, for example, by spin coating, or by means of any desiredprinting process, such as, for example, ink-jet printing, LITI (lightinduced thermal imaging, thermal transfer printing), screen printing,flexographic printing, offset printing or nozzle printing. Solublecompounds, which are obtained, for example, by suitable substitution,are necessary for this purpose.

Also possible are hybrid processes, in which, for example, one or morelayers are applied from solution and one or more further layers areapplied by vapour deposition. Thus, it is possible, for example, toapply the emitting layer from solution and to apply theelectron-transport layer by vapour deposition.

These processes are generally known to the person skilled in the art andcan be applied by him without inventive step to organicelectroluminescent devices comprising the compounds according to theinvention.

The compounds according to the invention generally have very goodproperties on use in organic electroluminescent devices. In particular,the lifetime on use of the compounds according to the invention inorganic electroluminescent devices is significantly better compared withsimilar compounds in accordance with the prior art. The other propertiesof the organic electroluminescent device, in particular the efficiencyand the voltage, are likewise better or at least comparable.Furthermore, the compounds have a high glass transition temperature andhigh thermal stability.

The invention will now be explained in greater detail by the followingexamples, without wishing to restrict it thereby.

A) SYNTHESES EXAMPLES

The following syntheses are carried out, unless indicated otherwise,under a protective-gas atmosphere in dried solvents. The solvents andreagents can be purchased, for example, from Sigma-ALDRICH or ABCR. Thecorresponding CAS numbers are also indicated in each case from thecompounds known from the literature.

a) 2-(9-phenyl-9H-carbazol-3-yl)-1H-imidazo[4,5-f]quinoxaline

38 g (156 mmol) of 2-bromo-1H-imidazo[4,5-f]quinoxaline, 50 g (172 mmol)of N-phenylcarbazole-3-boronic acid and 36 g (340 mmol) of sodiumcarbonate are dissolved in 1000 ml of ethylene glycol dimethyl ether and280 mL of water.

1,8 g (1.5 mmol) of tetrakies(triphenylphosphin)-palladium(0) are addedto this suspension, and the reaction mixture is heated under refluxedfor 16 h. After cooling, the organic phase is separated off, filteredover silica gel, washed three times with 200 mL of water and thenconcentrated to dryness. The product is purified by means of columnchromatography on silica gel with toluene/heptane (1:2).

The yield is 41 g (100 mmol), corresponding to 66% of theory.

The following compounds are prepared anagously:

Educt 1 Educt 2 Product Yield a1

76% a2

71% a3

73% a5

65% a6

63% a7

61%

b) 1-diphenylboranyl-2,3-dimethyl-1H-pyrrolo[3,2-h]quinoline

42 g (216 mmol) of 2,3-dimethyl-1H-pyrrolo[3,2-h]quinoline and 78 g (320mmol) of triphenylborane are dissolved in 3000 ml of dry toluene andboiled under reflux for 50 h under inert gaz. The solvent is distilledoff under vacuum, purified by chromatography (acetylester/hexane, 1:5)and finally sublimed (purity 99.9%) in a high vacuum (p=5×10⁻⁷ mbar).

Yield: 48 g (133 mmol), 62% of the theory.

The following compounds are prepared analogously:

Educt 1 Educt 2 Product Yield d1

62% d2

64% d3

58% d4

50% d5

56% d6

61% d7

50% d8

49% d9

53% d10

48% d11

46% d12

55% d13

45% d14

46% d15

65% d16

47% d17

53% d19

66% d20

59% d21

57% d22

61% d23

66% d24

61% d25

50% d26

63%

B) FABRICATION OF OLEDS

The following examples E1 to E13 (see Table 1) show data of variousOLEDs.

Substrate pre-treatment of examples E1-E13: Glass plates with structuredITO (50 nm, indium tin oxide) form the substrates on which the OLEDs areprocessed. Before evaporation of the OLED materials, the substrates arepre-baked for 15 minutes at 250° C., followed by an O₂ and subsequentArgon plasma treatment.

The OLEDs have in principle the following layer structure:substrate/hole-transport layer (HTL)/optional interlayer(IL)/electron-blocking layer (EBL)/emission layer (EML)/optionalhole-blocking layer (HBL)/electron-transport layer (ETL)/optionalelectron-injection layer (EIL) and finally a cathode. The cathode isformed by an aluminium layer with a thickness of 100 nm. The exact layerstructure is denoted in Table 1. The materials used for the OLEDfabrication are presented in Table 2.

All materials are applied by thermal vapour deposition in a vacuumchamber. The emission layer here always consists of at least one matrixmaterial (host material) and an emitting dopant (emitter), which isadmixed with the matrix material or matrix materials in a certainproportion by volume by co-evaporation. An expression such asIC1:M1:TEG1 (55%:35%:10%) here means that material IC1 is present in thelayer in a proportion by volume of 55%, M1 is present in the layer in aproportion of 35% and TEG1 is present in the layer in a proportion of10%. Analogously, the electron-transport layer may also consist of amixture of two materials.

The OLEDs are characterised by standard methods. The electroluminescence(EL) spectra are recorded at a luminous density of 1000 cd/m² and theCIE 1931 x and y coordinates are then calculated from the EL spectrum.

The examples E1-E13 show data of inventive OLEDs.

Use of Inventive Compounds as Host Material in Phosphorescent OLEDs

The use of the inventive materials EG1 to EG11 as host material inphosphorescent red OLEDs (experiments E1 to E11) results in anelectroluminescent emission with the color coordinates CIEx=0.67 andCIEy=0.33. This shows that the inventive materials are suitable for theuse in OLEDs.

TABLE 1 OLED layer structure HIL HTL EBL EML ETL Bsp. Dicke Dicke DickeDicke Dicke E1 HATCN SpMA1 SpMA3 IC5:EG1:TER5 ST2:LiQ 5 nm 125 nm 10 nm(45%:40%:5%) (50%:50%) 40 nm 35 nm E2 HATCN SpMA1 SpMA3 IC5:EG2:TER5ST2:LiQ 5 nm 125 nm 10 nm (45%:40%:5%) (50%:50%) 40 nm 35 nm E3 HATCNSpMA1 SpMA3 IC5:EG3:TER5 ST2:LiQ 5 nm 125 nm 10 nm (45%:40%:5%)(50%:50%) 40 nm 35 nm E4 HATCN SpMA1 SpMA3 IC5:EG4:TER5 ST2:LiQ 5 nm 125nm 10 nm (45%:40%:5%) (50%:50%) 40 nm 35 nm E5 HATCN SpMA1 SpMA3IC5:EG5:TER5 ST2:LiQ 5 nm 125 nm 10 nm (45%:40%:5%) (50%:50%) 40 nm 35nm E6 HATCN SpMA1 SpMA3 IC5:EG6:TER5 ST2:LiQ 5 nm 125 nm 10 nm(45%:40%:5%) (50%:50%) 40 nm 35 nm E7 HATCN SpMA1 SpMA3 IC5:EG7:TER5ST2:LiQ 5 nm 125 nm 10 nm (45%:40%:5%) (50%:50%) 40 nm 35 nm E8 HATCNSpMA1 SpMA3 IC5:EG8:TER5 ST2:LiQ 5 nm 125 nm 10 nm (45%:40%:5%)(50%:50%) 40 nm 35 nm E9 HATCN SpMA1 SpMA3 IC5:EG9:TER5 ST2:LiQ 5 nm 125nm 10 nm (45%:40%:5%) (50%:50%) 40 nm 35 nm E10 HATCN SpMA1 SpMA3IC5:EG10:TER5 ST2:LiQ 5 nm 125 nm 10 nm (45%:40%:5%) (50%:50%) 40 nm 35nm E11 HATCN SpMA1 SpMA3 IC5:EG11:TER5 ST2:LiQ 5 nm 125 nm 10 nm(45%:40%:5%) (50%:50%) 40 nm 35 nm

TABLE 2 Chemical structures of the OLED materials

The invention claimed is:
 1. A compound of the formula (1),

where the following applies to the symbols and indices used: Ar¹ isselected from the groups of formulae (Ar1-1) or (Ar1-2),

where the sign * indicates the position of the coordination to the Boronand the sign {circumflex over ( )} indicates the bonds to the adjacent6-membered ring, as depicted in formula (1); X stands, on eachoccurrence, identically or differently, for CR² or N; or two adjacentgroups X form together a ring condensed on the structure of formula (1),wherein the condensed ring is selected from an aryl or heteroaryl grouphaving 5 to 30 aromatic ring atoms, which may be substituted by one ormore radicals R²; Ar^(B) is, on each occurrence, identically ordifferently, an aromatic or heteroaromatic ring system having 5 to 60aromatic ring atoms, which may be substituted by one or more radicalsR³; W is on each occurrence, identically or differently, CR¹ or N; ortwo adjacent groups W stand for a group of formula (W-1) or (W-2),

where the dashed bonds indicate the bonding to the groups of formula(1); Z is on each occurrence, identically or differently, CR¹ or N; E¹,E² are, on each occurrence, identically or differently, selected from asingle bond, B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰, C═C(R⁰)₂, O, S, S═O,SO₂, N(R⁰), P(R⁰) and P(═O)R⁰, where at least one of the groups E¹ andE², present in the same ring, is not a single bond; R⁰ stands on eachoccurrence, identically or differently, for H, D, F, Cl, Br, I, CN, astraight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atomsor branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40C atoms, each of which may be substituted by one or more radicals R⁴,where in each case one or more non-adjacent CH₂ groups may be replacedby R⁴C═CR⁴, C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴),SO, SO₂, O, S or CONR⁴ and where one or more H atoms may be replaced byD, F, Cl, Br, I, CN or NO₂, an aromatic or heteroaromatic ring systemshaving 5 to 60 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴, or an aryloxy groups having 5 to60 aromatic ring atoms, which may be substituted by one or more radicalsR⁴, where two adjacent substituents R⁰ may form an aliphatic or aromaticring system together, which may be substituted by one or more radicalsR⁴; R¹, R², R³ stand on each occurrence, identically or differently, forH, D, F, Cl, Br, I, CHO, CN, C(═O)Ar³, P(═O)(Ar³)₂, S(═O)Ar³, S(═O)₂Ar³,N(Ar³)₂, NO₂, Si(R⁴)₃, B(OR⁴)₂, OSO₂R⁴, a straight-chain alkyl, alkoxyor thioalkyl groups having 1 to 40 C atoms or branched or a cyclicalkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of whichmay be substituted by one or more radicals R⁴, where in each case one ormore non-adjacent CH₂ groups may be replaced by R⁴C═CR⁴, C≡C, Si(R⁴)₂,Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴), SO, SO₂, O, S or CONR⁴ andwhere one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO₂,an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ringatoms, which may in each case be substituted by one or more radicals R⁴,or an aryloxy groups having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴; where two adjacent substituentsR¹, two adjacent substituents R² and/or two adjacent substituents R³ mayform an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴; Ar³ is, on each occurrence,identically or differently, an aromatic or heteroaromatic ring systemhaving 5 to 60 aromatic ring atoms, which may in each case also besubstituted by one or more radicals R⁴; R⁴ stands on each occurrence,identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chainalkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched orcyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, wherein each case one or more non-adjacent CH₂ groups may be replaced by SO,SO₂, O, S and where one or more H atoms may be replaced by D, F, Cl, Bror I, or an aromatic or heteroaromatic ring system having 5 to 24 Catoms.
 2. The compound according to claim 1, characterized in that Xstands, on each occurrence, identically or differently, for CR² or N; ortwo adjacent groups X form together a ring condensed on the structure offormula (1), wherein the condensed ring is selected from formulae (X-1)to (X-2),

where the dashed bonds indicate the bonding of the correspondingadjacent groups X to the structure of formula (1); V is on eachoccurrence, identically or differently, CR² or N; or two adjacent groupsV form together a ring condensed on the structure of formula (X-1) orformula (X-2), wherein the condensed ring is selected from formulae(V-1) and (V-2),

where: the dashed bonds indicate the bonding of the correspondingadjacent groups U to the structures of formulae (X-1) and (X-2); U is oneach occurrence, identically or differently, CR² or N; E¹, E² and R²have the same meaning as in claim
 1. 3. The compound according to claim1, characterized in that it is selected from the compounds of formula(2),

where the symbols Ar^(B), X and W have the same meaning as in claim 1.4. The compound according to claim 2, characterized in that it isselected from the compounds of formulae (3) to (6),

where Ar^(B) is, on each occurrence, identically or differently, anaromatic or heteroaromatic ring system having 5 to 60 aromatic ringatoms, which may be substituted by one or more radicals R³; W is on eachoccurrence, identically or differently, CR¹ or N; or two adjacent groupsW stand for a group of formula (W-1) or (W-2),

where the dashed bonds indicate the bonding to the groups of formula(1); Z is on each occurrence, identically or differently, CR^(l) or N;E¹, E² are, on each occurrence, identically or differently, selectedfrom a single bond, B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰, C═C(R⁰)₂, O, S,S═O, SO₂, N(R⁰), P(R⁰) and P(═O)R⁰, where at least one of the groups E¹and E², present in the same ring, is not a single bond; R⁰ stands oneach occurrence, identically or differently, for H, D, F, Cl, Br, I, CN,a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 Catoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3to 40 C atoms, each of which may be substituted by one or more radicalsR⁴, where in each case one or more non-adjacent CH₂ groups may bereplaced by R⁴C═CR⁴, C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se,P(═O)(R⁴), SO, SO₂, O, S or CONR⁴ and where one or more H atoms may bereplaced by D, F, Cl, Br, I, CN or NO₂, an aromatic or heteroaromaticring systems having 5 to 60 aromatic ring atoms, which may in each casebe substituted by one or more radicals R⁴, or an aryloxy groups having 5to 60 aromatic ring atoms, which may be substituted by one or moreradicals R⁴, where two adjacent substituents R⁰ may form an aliphatic oraromatic ring system together, which may be substituted by one or moreradicals R⁴; R¹, R², R³ stand on each occurrence, identically ordifferently, for H, D, F, Cl, Br, I, CHO, CN, C(═O)Ar³, P(═O)(Ar³)₂,S(═O)Ar³, S(═O)₂Ar³, N(Ar³)₂, NO₂, Si(R⁴)₃, B(OR⁴)₂, OSO₂R⁴, astraight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atomsor branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40C atoms, each of which may be substituted by one or more radicals R⁴,where in each case one or more non-adjacent CH₂ groups may be replacedby R⁴C═CR⁴, C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴),SO, SO₂, O, S or CONR⁴ and where one or more H atoms may be replaced byD, F, Cl, Br, I, CN or NO₂, an aromatic or heteroaromatic ring systemshaving 5 to 60 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴, or an aryloxy groups having 5 to60 aromatic ring atoms, which may be substituted by one or more radicalsR⁴; where two adjacent substituents R¹, two adjacent substituents R²and/or two adjacent substituents R³ may form an aliphatic or aromaticring system together, which may be substituted by one or more radicalsR⁴; Ar³ is, on each occurrence, identically or differently, an aromaticor heteroaromatic ring system having 5 to 60 aromatic ring atoms, whichmay in each case also be substituted by one or more radicals R⁴; R⁴stands on each occurrence, identically or differently, for H, D, F, Cl,Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groupshaving 3 to 20 C atoms, where in each case one or more non-adjacent CH₂groups may be replaced by SO, SO₂, O, S and where one or more H atomsmay be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromaticring system having 5 to 24 C atoms and the symbol V has the same meaningas in claim
 2. 5. The compound according to claim 1, characterized inthat the compound is selected from the compounds of formulae (3-1) to(6-2),

where the symbols Ar^(B), R¹ and R² have the same meaning as in claim 1and where E¹ in formula (6-1) is B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰,C═C(R⁰)₂, O, S, S═O, SO₂, N(R⁰), P(R⁰) or P(═O)R⁰, with R⁰ having thesame meaning as in claim
 1. 6. The compound according to claim 1,characterized in that the group Ar^(B) is selected from aromatic orheteroaromatic ring systems having 5 to 18 C atoms, each of which may besubstituted by one or more radicals R³.
 7. The compound according toclaim 1, characterized in that the compound comprises at least one groupR¹ or R² selected from aromatic or heteroaromatic ring systems having 5to 60 aromatic ring atoms, which may in each case be substituted by oneor more radicals R⁴.
 8. The compound according to claim 1, characterizedin that the compound comprises at least one group R¹ or R² selected fromthe groups of formulae (R-1) to (R15),

where: the dashed bond indicates the bonding to the structure of formula(1) and V is on each occurrence, identically or differently, CR² or N;or two adjacent groups V form together a ring condensed on the structureof formula (X-1) or formula (X-2), wherein the condensed ring isselected from formulae (R-6) to (R-15),

where: the dashed bonds indicate the bonding of the correspondingadjacent groups U to the structures of formulae (R-6) to (R-15); U is oneach occurrence, identically or differently, CR² or N; E¹, E² and R²have the same meaning as in claim 1; with the proviso that V is a C atomwhen the dashed bond is bonded to V, and where: R^(N), R^(C) are on eachoccurrence, identically or differently, H, D, F, Cl, Br, I, CHO,N(Ar³)₂, C(═O)Ar³, P(═O)(Ar³)₂, S(═O)Ar³, S(═O)₂Ar³, (R)C═C(R)Ar³, CN,NO₂, Si(R⁴)₃, B(OR⁴)₂, B(R⁴)₂, B(N(R⁴)₂)₂, OSO₂R⁴, a straight-chainalkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or astraight-chain alkenyl or alkynyl group having 2 to 40 C atoms or abranched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy grouphaving 3 to 40 C atoms, each of which may be substituted by one or moreradicals R⁴, where one or more, preferably non-adjacent CH₂ groups maybe replaced by (R⁴) C═C(R⁴), C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S,C═Se, P(═O)(R⁴), SO, SO₂, N(R⁴), O, S or CON(R⁴) and where one or more Hatoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system having 5 to 60 aromatic ring atoms, which mayin each case be substituted by one or more radicals R⁴, or an aryloxy orheteroaryloxy group having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴, where optionally two adjacentsubstituents R^(C) can form a mono- or polycyclic, aliphatic, aromaticor heteroaromatic ring system with one another; where Ar³ and R⁴ havethe same definitions as in claim 1; and T stands, on each occurrence,identically or differently, for CR⁴ or N, with the proviso that T is a Catom when the dashed bond is bonded to T; or two adjacent groups T standfor a group of formula (T-1) or (T-2),

where the dashed bonds in formulae (T-1) and (T-2) indicate the bondingto the groups of formulae (R-1) to (R-5); and where E¹, E² have the samemeaning as in claim 1; G is on each occurrence, identically ordifferently, CR⁴ or N; where R⁴ has the same meaning as in claim 1; L isan aromatic or heteroaromatic ring system having 5 to 30 aromatic ringatoms, which may be substituted by one or more radicals R⁴; and n is 0or
 1. 9. A process for the preparation of the compound of formula (1) asclaimed in claim 1, characterized in that a compound of formula (Int)reacts with a triarylborane B(Ar^(B))₃ so that a compound of formula (1)is obtained:

where the symbols Ar¹, Ar^(B), W and X have the same meaning as inclaim
 1. 10. An organic electroluminescent device, characterised in thatthe compound according to claim 1 is employed as a matrix material foremitters, a hole-transport-material or an electron-transport material.11. An organic electroluminescent devices comprising a cathode, an anodeand at least one emitting layer arranged between the anode and thecathode, wherein the at least one emitting layer comprises at least onephosphorescent material as an emitter and at least one compoundaccording to claim 1 as a matrix material.
 12. The electronic deviceaccording to claim 11, characterized in that the phosphorescent materialhas an emission wavelength comprised between 550 nm to 680 nm.
 13. Aformulation comprising at least one compound according to claim 1 and atleast one solvent.
 14. An electronic device comprising at least onecompound according to claim
 1. 15. A formulation comprising at least onecompound of the formula (1),

where the following applies to the symbols and indices used: Ar¹ is aheteroaryl group comprising at least one nitrogen which is representedin formula (1), having 5 to 30 aromatic ring atoms, which may besubstituted by one or more radicals R¹; X stands, on each occurrence,identically or differently, for CR² or N; or two adjacent groups X formtogether a ring condensed on the structure of formula (1), wherein thecondensed ring is selected from an aryl or heteroaryl group having 5 to30 aromatic ring atoms, which may be substituted by one or more radicalsR²; Ar^(B) is, on each occurrence, identically or differently, anaromatic or heteroaromatic ring system having 5 to 60 aromatic ringatoms, which may be substituted by one or more radicals R³; W is on eachoccurrence, identically or differently, CR¹ or N; or two adjacent groupsW stand for a group of formula (W-1) or (W-2),

where the dashed bonds indicate the bonding to the groups of formula(1); Z is on each occurrence, identically or differently, CR¹ or N; E¹,E² are, on each occurrence, identically or differently, selected from asingle bond, B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰, C═C(R⁰)₂, O, S, S═O,SO₂, N(R⁰), P(R⁰) and P(═O)R⁰, where at least one of the groups E¹ andE², present in the same ring, is not a single bond; R⁰ stands on eachoccurrence, identically or differently, for H, D, F, Cl, Br, I, CN, astraight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atomsor branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40C atoms, each of which may be substituted by one or more radicals R⁴,where in each case one or more non-adjacent CH₂ groups may be replacedby R⁴C═CR⁴, C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴),SO, SO₂, O, S or CONR⁴ and where one or more H atoms may be replaced byD, F, Cl, Br, I, CN or NO₂, an aromatic or heteroaromatic ring systemshaving 5 to 60 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴, or an aryloxy groups having 5 to60 aromatic ring atoms, which may be substituted by one or more radicalsR⁴, where two adjacent substituents R⁰ may form an aliphatic or aromaticring system together, which may be substituted by one or more radicalsR⁴; R¹, R², R³ stand on each occurrence, identically or differently, forH, D, F, Cl, Br, I, CHO, CN, C(═O)Ar³, P(═O)(Ar³)₂, S(═O)Ar³, S(═O)₂Ar³,N(Ar³)₂, NO₂, Si(R⁴)₃, B(OR⁴)₂, OSO₂R⁴, a straight-chain alkyl, alkoxyor thioalkyl groups having 1 to 40 C atoms or branched or a cyclicalkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of whichmay be substituted by one or more radicals R⁴, where in each case one ormore non-adjacent CH₂ groups may be replaced by R⁴C═CR⁴, C≡C, Si(R⁴)₂,Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴), SO, SO₂, O, S or CONR⁴ andwhere one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO₂,an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ringatoms, which may in each case be substituted by one or more radicals R⁴,or an aryloxy groups having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴; where two adjacent substituentsR¹, two adjacent substituents R² and/or two adjacent substituents R³ mayform an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴; Ar³ is, on each occurrence,identically or differently, an aromatic or heteroaromatic ring systemhaving 5 to 60 aromatic ring atoms, which may in each case also besubstituted by one or more radicals R⁴; R⁴ stands on each occurrence,identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chainalkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched orcyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, wherein each case one or more non-adjacent CH₂ groups may be replaced by SO,SO₂, O, S and where one or more H atoms may be replaced by D, F, Cl, Bror I, or an aromatic or heteroaromatic ring system having 5 to 24 Catoms and at least one solvent.
 16. An electronic device comprising atleast one compound of the formula (1),

where the following applies to the symbols and indices used: Ar¹ is aheteroaryl group comprising at least one nitrogen which is representedin formula (1), having 5 to 30 aromatic ring atoms, which may besubstituted by one or more radicals R¹; X stands, on each occurrence,identically or differently, for CR² or N; or two adjacent groups X formtogether a ring condensed on the structure of formula (1), wherein thecondensed ring is selected from an aryl or heteroaryl group having 5 to30 aromatic ring atoms, which may be substituted by one or more radicalsR²; Ar^(B) is, on each occurrence, identically or differently, anaromatic or heteroaromatic ring system having 5 to 60 aromatic ringatoms, which may be substituted by one or more radicals R³; W is on eachoccurrence, identically or differently, CR¹ or N; or two adjacent groupsW stand for a group of formula (W-1) or (W-2),

where the dashed bonds indicate the bonding to the groups of formula(1); Z is on each occurrence, identically or differently, CR¹ or N; E¹,E² are, on each occurrence, identically or differently, selected from asingle bond, B(R⁰), C(R⁰)₂, Si(R⁰)₂, C═O, C═NR⁰, C═C(R⁰)₂, O, S, S═O,SO₂, N(R⁰), P(R⁰) and P(═O)R⁰, where at least one of the groups E¹ andE², present in the same ring, is not a single bond; R⁰ stands on eachoccurrence, identically or differently, for H, D, F, Cl, Br, I, CN, astraight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atomsor branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40C atoms, each of which may be substituted by one or more radicals R⁴,where in each case one or more non-adjacent CH₂ groups may be replacedby R⁴C═CR⁴, C≡C, Si(R⁴)₂, Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴),SO, SO₂, O, S or CONR⁴ and where one or more H atoms may be replaced byD, F, Cl, Br, I, CN or NO₂, an aromatic or heteroaromatic ring systemshaving 5 to 60 aromatic ring atoms, which may in each case besubstituted by one or more radicals R⁴, or an aryloxy groups having 5 to60 aromatic ring atoms, which may be substituted by one or more radicalsR⁴, where two adjacent substituents R⁰ may form an aliphatic or aromaticring system together, which may be substituted by one or more radicalsR⁴; R¹, R², R³ stand on each occurrence, identically or differently, forH, D, F, Cl, Br, I, CHO, CN, C(═O)Ar³, P(═O)(Ar³)₂, S(═O)Ar³, S(═O)₂Ar³,N(Ar³)₂, NO₂, Si(R⁴)₃, B(OR⁴)₂, OSO₂R⁴, a straight-chain alkyl, alkoxyor thioalkyl groups having 1 to 40 C atoms or branched or a cyclicalkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of whichmay be substituted by one or more radicals R⁴, where in each case one ormore non-adjacent CH₂ groups may be replaced by R⁴C═CR⁴, C≡C, Si(R⁴)₂,Ge(R⁴)₂, Sn(R⁴)₂, C═O, C═S, C═Se, P(═O)(R⁴), SO, SO₂, O, S or CONR⁴ andwhere one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO₂,an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ringatoms, which may in each case be substituted by one or more radicals R⁴,or an aryloxy groups having 5 to 60 aromatic ring atoms, which may besubstituted by one or more radicals R⁴; where two adjacent substituentsR¹, two adjacent substituents R² and/or two adjacent substituents R³ mayform an aliphatic or aromatic ring system together, which may besubstituted by one or more radicals R⁴; Ar³ is, on each occurrence,identically or differently, an aromatic or heteroaromatic ring systemhaving 5 to 60 aromatic ring atoms, which may in each case also besubstituted by one or more radicals R⁴; R⁴ stands on each occurrence,identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chainalkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched orcyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, wherein each case one or more non-adjacent CH₂ groups may be replaced by SO,SO₂, O, S and where one or more H atoms may be replaced by D, F, Cl, Bror I, or an aromatic or heteroaromatic ring system having 5 to 24 Catoms.
 17. The electronic device according to claim 16, characterized inthat the device is selected from the group consisting of organicelectroluminescent devices, organic integrated circuits, organicfield-effect transistors, organic thin-film transistors, organiclight-emitting transistors, organic solar cells, dye-sensitised organicsolar cells, organic optical detectors, organic photoreceptors, organicfield-quench devices, light-emitting electrochemical cells, organiclaser diodes and organic plasmon emitting devices.